A nighttime view of a residential area with houses adorned with holiday lights.

Find Hotels with a Pool in Stockbridge, MA

Check availability on Stockbridge Hotels with a Pool

Next weekend
Jul 31 - Aug 2
In two weeks
Aug 7 - Aug 9

Our top choices for Stockbridge hotels with a pool

Outdoor pool, sun loungers

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,008 reviews)
  • cleanliness
    Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
$226 nightly
The price is $252
Jul 27 - Jul 28
Total with taxes and fees
The Red Lion Inn
Seasonal outdoor pool, open 9:00 AM to 6:00 PM, sun loungers

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
4.5 star property
Stockbridge
9.2 out of 10, Wonderful, (113 reviews)
  • cleanliness
    Seasonal outdoor pool retreat at this colonial b&b invites lounging amid gardens and historic charm.
$358 nightly
The price is $399
Aug 9 - Aug 10
Total with taxes and fees
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Seasonal outdoor pool

The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Stockbridge
9.8 out of 10, Exceptional, (99 reviews)
  • cleanliness
    Seasonal outdoor pool beckons for refreshing summer dips at this upscale bed and breakfast in Stockbridge.
$389 nightly
The price is $435
Jul 27 - Jul 28
Total with taxes and fees
The Inn at Stockbridge
2 indoor pools, 2 outdoor pools, pool umbrellas, sun loungers

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 star property
South Lee
9.2 out of 10, Wonderful, (942 reviews)
  • cleanliness
    Float in mountain serenity at four incredible pools offering a perfect family-friendly oasis.
$157 nightly
The price is $175
Aug 25 - Aug 26
Total with taxes and fees
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Indoor pool, outdoor pool, open 8:00 AM to 10:00 PM, sun loungers

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,020 reviews)
  • cleanliness
    Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
$170 nightly
The price is $190
Jul 27 - Jul 28
Total with taxes and fees
The Yankee Inn
Indoor pool

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
3.0 star property
Great Barrington
9.4 out of 10, Exceptional, (797 reviews)
  • cleanliness
    Refreshing indoor pool sanctuary near Ski Butternut lets guests swim year-round after mountain adventures.
$195 nightly
The price is $217
Aug 10 - Aug 11
Total with taxes and fees
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Indoor pool

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
Great Barrington
8.8 out of 10, Excellent, (794 reviews)
  • cleanliness
    Relax in this riverside hotel with an indoor heated pool, where ski-day recovery meets year-round aquatic enjoyment.
$140 nightly
The price is $156
Aug 23 - Aug 24
Total with taxes and fees
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Indoor pool

Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
3.0 star property
Lenox
9.2 out of 10, Wonderful, (640 reviews)
  • cleanliness
    Dive into year-round aquatic relaxation at this Berkshires retreat with a sparkling indoor pool and modern fitness center.
$229 nightly
The price is $255
Aug 13 - Aug 14
Total with taxes and fees
Courtyard by Marriott Lenox Berkshires
Indoor pool, open 8:00 AM to 10:00 PM, sun loungers

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,004 reviews)
  • cleanliness
    Splash into art deco luxury at this indoor pool sanctuary, where relaxation meets mountain adventure.
$180 nightly
The price is $201
Aug 23 - Aug 24
Total with taxes and fees
Hampton Inn & Suites Berkshires-Lenox
Outdoor pool, sun loungers

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (139 reviews)
  • cleanliness
    Escape to an elegant countryside retreat with an inviting outdoor pool, premium spa services, and made-to-order gourmet breakfast.
$409 nightly
The price is $457
Aug 25 - Aug 26
Total with taxes and fees
Devonfield Inn B&B
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties

Choose what matters most at hotels with a pool in Stockbridge

Breakfast included
Hot tub

Top Stockbridge Hotel Reviews

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"Perfect for my needs. The Mint restaurant has delicious Indian food with a beautiful view. I was able to rent a kayak the morning I was leaving and they were flexible with check out time."
Maura 1-night trip
Posted 2 days ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Frequently asked questions

What are the best hotels in Stockbridge with outdoor pools?
The Red Lion Inn is a charming 3.5-star hotel that offers an inviting outdoor pool, great for families looking to unwind after a day of adventure in the beautiful Berkshires. Guests rave about the comfortable and quiet rooms, as well as the excellent food and friendly service provided by the staff. Plus, its prime location in a historic district means you're just a stone's throw away from local attractions, including nearby ski areas for winter sports enthusiasts.

For a more intimate experience, consider The Stockbridge Country Inn, rated 4.5 stars by travellers. This delightful bed and breakfast not only features an outdoor pool but also provides complimentary full and continental breakfasts, ensuring a great start to your day. With its proximity to the Norman Rockwell Museum and picturesque mountain views, it's an ideal spot for families seeking both relaxation and cultural enrichment. Guests particularly appreciate the peaceful atmosphere and the opportunity for mountain biking right on-site.
How much does a hotel with outdoor pool in Stockbridge cost?
Enjoy staying in a hotel in Stockbridge with an outdoor pool. You can find a great deal from $156 on Expedia. If you're leaning toward a little luxury, prices can rise, and may vary depending on the location, season, and hotel amenities. Be sure to book in advance to enjoy more options and potentially better rates, especially if you're planning a trip during weekends or around public holidays.
Is it cheaper to book flights and a Stockbridge hotel with a pool as a package?
Booking a hotel and flight package on Expedia can be cheaper than booking flights and hotels separately. Bundling can lead to significant savings, especially for international travel or when booking well in advance. However, savings vary depending on factors like destination, travel dates and availability, so it's wise to compare options. With access to over 300,000 hotels worldwide, Expedia makes it easy to build the perfect vacation package.
Can I cancel my hotel reservation on Expedia?
Expedia has plenty of refundable hotels. In many cases, you need to cancel your booking 24-48 hours ahead of your arrival date. Remember to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use Expedia's "Fully refundable property" filter during your search to find the right hotel in Stockbridge for you.

Explore a world of travel with Expedia